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Method for preparing linagliptin intermediate for treating II-type diabetis

A technology for intermediates and diabetes, which is applied in the field of drug synthesis, can solve the problems of increased risk, difficult handling, and increased post-processing workload, etc., and achieves the effects of mild conditions, good selection, and avoidance of dangerous and toxic reagents

Active Publication Date: 2016-09-28
段敏
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The technical effect of this new technology can include improved performance or efficiency compared with existing technologies for certain applications such as heating systems that use electricity alone (Etherm).

Problems solved by technology

Technological Problem: Current methods for producing lindopeptins involve complicated processes involving multiple steps like starting materials from different sources, chemical synthetic techniques, crystallographics analysis, and other technical problem addressed in the patented text.

Method used

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  • Method for preparing linagliptin intermediate for treating II-type diabetis

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Embodiment 1

[0022] A method for preparing a linagliptin intermediate for the treatment of type II diabetes, comprising the following steps:

[0023] Under nitrogen protection, 8.1g (60mmol) of copper chloride, 7.2g (40mmol) of o-phenanthroline and 8-bromo-3,7-dihydro-3-methyl-1H-purine-2,6-dione 24.5g (100mmol) was dissolved in 150ml DMF, then the DMF solution of 2-butyne (containing 2-butyne 8.6g, 160mmol) was added dropwise, reacted at 40°C for 5 hours, then the reaction solution was poured into water, extracted with DCM, Wash with saturated brine, dry over anhydrous sodium sulfate, concentrate, then recrystallize in a mixed solvent of petroleum ether and DCM with a volume ratio of 40:1, filter, and dry to obtain the intermediate 8-bromo-3,7- Dihydro-3-methyl-9-(2-butynyl)-1H-purine-2,6-dione 26.8g, yield 90.2%, purity 99.92% (HPLC area normalization method).

Embodiment 2

[0025] A method for preparing a linagliptin intermediate for the treatment of type II diabetes, comprising the following steps:

[0026] Under nitrogen protection, 9.4g (70mmol) of copper chloride, 7.2g (40mmol) of o-phenanthroline and 8-bromo-3,7-dihydro-3-methyl-1H-purine-2,6-dione 24.5g (100mmol) was dissolved in 150ml DMF, then the DMF solution of 2-butyne (containing 2-butyne 7.6g, 140mmol) was added dropwise, reacted at 50°C for 6 hours, then the reaction solution was poured into water, extracted with DCM, Wash with saturated brine, dry over anhydrous sodium sulfate, concentrate, then recrystallize in a mixed solvent of petroleum ether and DCM with a volume ratio of 45:1, filter, and dry to obtain the intermediate 8-bromo-3,7- Dihydro-3-methyl-9-(2-butynyl)-1H-purine-2,6-dione 27.1 g, yield 91.1%, purity 99.97% (HPLC area normalization method).

Embodiment 3

[0028] A method for preparing a linagliptin intermediate for the treatment of type II diabetes, comprising the following steps:

[0029] Under nitrogen protection, 6.7g (50mmol) of copper chloride, 9g (50mmol) of o-phenanthroline and 24.5 g of 8-bromo-3,7-dihydro-3-methyl-1H-purine-2,6-dione g (100mmol) was dissolved in 150ml DMF, then the DMF solution of 2-butyne (containing 2-butyne 9.7g, 180mmol) was added dropwise, reacted at 45°C for 5 hours, then the reaction solution was poured into water, extracted with DCM, saturated Wash with brine, dry over anhydrous sodium sulfate, concentrate, then recrystallize in a mixed solvent of petroleum ether and DCM with a volume ratio of 40:1, filter, and dry to obtain the intermediate 8-bromo-3,7-di Hydrogen-3-methyl-9-(2-butynyl)-1H-purine-2,6-dione 26.7g, yield 89.7%, purity 99.89% (HPLC area normalization method).

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Abstract

The invention discloses a method for preparing a linagliptin intermediate for treating II-type diabetis. The method comprises the following steps: enabling 8-bromo-3,7-dihydro-3-methyl-1H-purine-2,6-diketone to react with 2-butyne in DMF (Dimethyl Formamide) under the protection of nitrogen and the existence of copper chloride and phenanthroline, thus generating the linagliptin intermediate 8-bromo-3,7-dihydro-3-methyl-9-(2-butynyl)-1H-purine-2,6-diketone. The method for preparing the linagliptin intermediate, disclosed by the invention, is simple, the conditions are gentle, the selectivity is better, and dangerous and toxic reagents are prevented from being used.

Description

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Claims

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Application Information

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Owner 段敏
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